Hydrochloric Acid → HCID 57517323, compound

Participants

Reaction Steps

To a solution of 4-chloro-3-methyl-benzonitrile (5 g, 33 mmol) in benzene (100 mL) was slowly added isopropylmagnesium bromide (1 M in THF, 66 mL, 66 mmol) at room temperature. The solution was then heated to reflux for 3 hours. After cooling in an ice bath, the reaction mixture was carefully treated with 6 M HCl (52 mL). It was then heated to reflux for 2 hours with vigorous mechanical stirring. The mixture was allowed to cool to room temperature, diluted with Et2O (100 mL) and washed with water and brine. The organic layer was dried over sodium sulfate, filtered and concentrated. The crude was purified by Kugelrohr distillation (110-130° C./0.1 Torr). Contaminated fractions were further purified by chromatography on silica gel (cyclohexane/EtOAc).

Provenance & Evidence